Ammonia → HCID 68549497, compound

HRID 2189939Notes

Reaction equation

HRID 2189939 reaction equation
[ClH:1].[C:2](=[NH:6])([NH2:5])[CH2:3][CH3:4].[F:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:9]=1[C:15]1[S:19][C:18](CCC#N)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:17]([C:30](=[O:35])[C@@H:31]([O:33][CH3:34])[CH3:32])[N:16]=1.Cl.N>C(O)C>[ClH:1].[F:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:9]=1[C:15]1[S:19][C:18]([CH2:4][CH2:3][C:2](=[NH:5])[NH2:6])([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:17]([C:30](=[O:35])[C@@H:31]([O:33][CH3:34])[CH3:32])[N:16]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 12301253Propionimidamide hydrochlorideHCID 68549380HCID 68549380, compound

Product 1

HCID 68549497HCID 68549497, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

Preparation of 345-(2,5-difluorophenyl)-3-((S)-2-methoxypropanoyl)-2-phenyl-2,3-dihydro-1,3,4-thiadiazol-2-yl)propanimidamide hydrochloride: To a cooled (0° C.) solution of 3-(5-(2,5-difluorophenyl)-3-((S)-2-methoxypropanoyl)-2-phenyl-2,3-dihydro-1,3,4-thiadiazol-2-yl)propanenitrile (0.053 g, 0.13 mmol) in ethanol (0.5 mL) was added a 9.8 M solution of ethanolic HCl (0.5 mL). After stirring at 0° C. for 10 minutes and then at room temperature for 4 hours, the reaction mixture was concentrated under reduced pressure. To the residue was added NH3 (1.0 mL, 7.0 mmol, 7 M solution in methanol). After stirring at room temperature for 30 minutes, the mixture was concentrated under reduced pressure. The residue was chromatographed (dichloromethane followed by 20% MeOH and 1% aqueous NH4OH in dichloromethane) to afford the product as a mixture of diastereomers (3.4 mg, 15% yield). MS ESI (+) m/z 433 (M+1) detected; 1H NMR (400 MHz, CDCl3) δ 9.0 (br, 4H), 8.7 (br, 4H), 7.51 (m, 2H), 7.38 (m, 8H), 7.32 (m, 2H), 7.14 (m, 4H), 4.73 (m, 2H), 3.57 (m, 2H), 3.42 (s, 3H), 3.35 (s, 3H), 2.75 (m, 4H), 2.33 (m, 1H), 2.23 (m, 1H), 1.52 (d, 3H, J=6.3 Hz), 1.48 (d, 3H, J=7.0 Hz).

Workup

  1. waitat room temperature for 4 hours
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. stirringAfter stirring at room temperature for 30 minutes
  4. concentrationthe mixture was concentrated under reduced pressure
  5. customThe residue was chromatographed (dichloromethane followed by 20% MeOH and 1% aqueous NH4OH in dichloromethane)
  6. customto afford the product
  7. additionas a mixture of diastereomers (3.4 mg, 15% yield)

Sources & evidence

ORD record
ord-b842bb4cb2204e12aed7ac98ab32d111
Source dataset
uspto-grants-2012_12
Patent number
US08324257B2

Reaction notes

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